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A study involving 333 adolescents aged from 13 to 17 was carried out to investigate whether or not self-esteem mediates the relationship between sex and gender role attitudes, and to investigate several factors which might be related to self-esteem and to attitudes toward gender roles. Gender-role self-attributions and socio-demographic factors were considered. Young female adolescents with low levels of positive feminine attributes and high levels of negative feminine attributes were most likely to have low self-esteem; young male adolescents with low levels of feminine characteristics were most likely to hold stereotyped attitudes to gender roles. Self-esteem was not found to be a moderator of gender role attitudes, and gender roles made a considerable contribution to the variance in self-esteem. The results are discussed with regard to the contribution of negative gender characteristics to well-being, and the lack of discrimination between females and males shown by these negative scales. It is suggested that negative “feminine” characteristics are equally undesirable for girls and boys, and that it is no longer appropriate to give them a gender label.